Mono-azo dyestuffs



Patented May 2, 1944 MONO-AZO' DYESTUFFS Grald Bonhote, deceased, late of Basel, Switzerland, by Marcelle Bonhote, administratrix, Saint Blaise, Switzerland, and Ernst Alfred Henzi, Basel, Switzerland, assignors to Society I of Chemical Industry in Basle, Basel, Switzerland No Drawing. Application January 16,1942, Serial No. 427,066. In Switzerland October 1P7, 1940 3 Claims. (01. 2 60-198) wherein at least one :u and not more than two ys stand for SOsH-groups, wherein, if only one 1 stands for a SOaH-group, this stands in one of the positions 4, 5 and 6, and wherein finally if two ys stand for SOaH-groups, these'are separated by at least one :11 standing for a'hydrogen' atom. Aminonaphthol sulfonic acidsfrom which such compounds are obtained, are for example the 1 amino-8-hydroxynaphthalene-4-sulfonic acid, the 1-amino-8-hydroxynaphthalene-6-sulionic acid, the 1-amino-S-hydroxynaphthalene- 3:6-disulfonic acid and the l-amino-S-hydroxy- I naphthalene-4 G-disulfonic acid, whereas the acyl radical may be an N-acetyl, an N-chloroacetyl, an N-carboxyethyl, an N-benzoyl, an N-chlorobenzoyl, an N-methoxybenzoyl, an N-phenoxyacetyl, an N-benzenesulfonyl, anN-para-toluenesulfonyl, and an N-para-chlorobenzene sulfonyl or a 1- or Z-naphthalene sulfonyl radical.

Among the monodiazo compounds of the diphenyl series, the diazo compoundsobtainable from the following substances may be mentioned: 2-aminodiphenyl, 4-aminodiphenyl, 4-amino-4'- acetylaminodiphenyl, 2-amino-4:4'-diacetylaminodiphenyl, 4-amino-4-acetylaminodiphenyl, 4- amin0-2' 5-dimethoxydiphenyl, 4-amino-3 :2 5- trimethoxy-6-chlorodiphenyl, 4-amino-3 :3 '-dimethoxy-4'-acetylaminodiphenyl.

se .dre t fls. a e. j Re ular y val h ch are derived from N-acylated amino-naphthol sul- I fonic acids of the general formula I H (I) III acyl wherein one stands for a hydrogen atom and the other 1 stands for a sOsH-group; among these, especially, those which are derived from diazotizing components of the type of the Z-aminodiphenylenes. Among the latter dyestufl's those are particularly valuable in which acyl represents a SOz-ary1 radical, aryl standing for an aryl nucleus of the benzene series. The new dyestufis cannot only be used for the preparation of dyeings on textiles; they may also find other applications, such as in the manufacture of colored lacquers, etc. o V

The following examples illustrate the invention, the parts being by weight:

Example 1 is a red powder which dissolves in concentrated sulfuric acid with a red coloration and dyes wool in-very pure, bluish-red shades from acid dyebauw l v o, ..v ,7

Example 2 commences at once, and when t is complete 'the.

precipitated dyestufi is filtefed oiil After clr ing, the dyestufi is obtained in the form ,ofa violet-brown powder which dissolves to a bluish- Dyestufi No. 4 of the above table corresponds in the free form to the formula Dye stuiT; No, 12o; the above table corresponds in the free form tothe formula violet solution in concentratedsulfuric acid and dyes wool in pure violet sli form to the formula G- e HaCENH-O-N=N 03H SOaH Example 3 0.2 part of the dyestufi obtained in Example 1 st 'i-mm tdyee baths. The new dyestufi corresponds in the free Dyes fit 4? Q t e. e wq b c re s in the free form to the formula is dissolved in 400 parts of water, and 1 part of 30 sodium sulfate cryst. is added to this solution. H- o r V lujparts of wool are entered into the dyer-bath HO I QLO thus} obtainedf 0.4 Part; of concentrated formic 9 acid is-added to the bath, which is then raised to a the 'boiling point, and dyeing is carried outfor 1 35 hour at 955100 C. Aftertrinsingn and drying, an SOBH SO3H eitraprdinary pure bluish-red dyeing is obtained. 7 The following table indicates the shades. which may be dyed upon wool by means of -thedyestuffs of thefp're'sent application H 40 l rizo component Diazo component Shad 1 'l-acetylamindiS-hvdIoXynaphthaIene V 4-aminodiphenyl Bluish r d, 2 do 2-an iinodipl ienyl 7 D 3 --do 4-amiu'o-2:5d1m6th Vloleh' 4 l-acetyla -hydroxynaphtha1enc-4-sulfonicacid. Z-aminod ipheny iBluih red; I l-acetylamino-8-hydroxynaphthalene-3:6disu1fonic acinL 4-aminoflip Do .5 Z-aminddip o. 4-ariiino 2j: '.-dim e oxy. p Violet.

8 4-ace y1mmMf-aminodiphen Do.v

4:4"-diacetylammo'-2 aminodip Bluish'red 4-arninoeij-oxalylarninodipl en BluislrBordeaux m ?d r 9ny V i shii v :"T 'T-"','4".!"-""'T""' D do Do.

-aminodiphenylinz D0 ne 'eflim thm i e 4-amino 4fcetylaminod p e'nyl un d. 4-amino3:%:fi -trimetfibxyoehlorodip en Do. 4z4{-diacotyliunino-Z-aniinodiphenyl Bluisl red;

4-amino-4 oxalylaminodiphenyl 'Bluish Bordeaux. (1 4-amino;4=oxa.lylamino,-3:3Gdime "Violet. i lzl-naphthalenesulfonylamm I I 2-arnmodiphenyluu, I Bluish red disulionicacid. 11 22.--. 1-(4'-}chloro)-benzene-sulionylamino-S-hydroxynaphthalenc- .-do;., .l 13

3:6-di8l1lf0ni0 aci A dip); qylnn Bluish Bordeaux 3' imethoxydiphenyl -Violg;.

Red." Blulshir'ed. Dor

ionic acid.

Violet, a 35.-.- l-benzoylamino-S-hydroxynaphthalcnc-BzG-disuliome ac1d B1l1iSh-f6d. n p v Bordeaux, :31 do Y Violefi l-benzoylamino-8-hydroxynaphthalencizfi disuliomc ac1d.--- t 531mm d. im we r kamanodiphenylu. I BgQdiShBOrdmuL 7 v. iiPPr'i-t QtWWH94iPlIEQ i e Dyestuff No. 25 of the above table corresponds in the free form to the formula l? OCH, OCH: H0 NS--=Cl I I ll 6 CH: 01 805E SOaH Dyestufr No. 35 of the above table corresponds in the free form to the formula Dyestufi No. 38 of the above table corresponds in the free form to the formula SOaH What We claim is: 1. The monoazo-dyestufis corresponding in the free form to the general formula H m I%I-S0nB1'yl R-N=N wherein aryl stands for a nucleus of the benzene series, and wherein one :1 stands for an SOaH- group and the other y stands for a hydrogen atom.

3. The monoazo-dyestuff corresponding in the free form to the formula SOaH MARCELLE BONHOTE, Administratrix of the Estate 01' Gerald Bonhte,

Deceased.

ERNST ALFRED HENZI. 

